91871-07-7Relevant academic research and scientific papers
Hantzsch Ester-Mediated Synthesis of Phenanthridines under Visible-Light Irradiation
Nagode, Savita B.,Kant, Ruchir,Rastogi, Namrata
, p. 3513 - 3518 (2020)
An efficient photocatalytic synthesis of phenanthridines mediated by an organo-photoredox initiator Hantzsch ester has been developed via denitrogenative intramolecular annulation of benzotriazolyl chalcones. The highly reducing photoactivated Hantzsch es
Direct photoexcitation of benzothiazolines: Acyl radical generation and application to access heterocycles
He, Xiang-Kui,Li, Lei,Lu, Juan,Xuan, Jun,Ye, Hai-Bing
, (2021/11/27)
An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules.
Photo-redox catalyzed dehydrazinative acylation of N-heterocycles: Via Minisci reaction
Hafeez, Saira,Saeed, Aamer
, p. 38683 - 38689 (2021/12/20)
Visible light-induced acylation of heteroaromatic compounds have been achieved using benzoyl hydrazides as an efficient acyl source under mild reaction conditions. The photo-redox catalyzed oxidative cleavage of hydrazides leads to in situ formation of ac
Selective C(sp3)-H activation of simple alkanes: visible light-induced metal-free synthesis of phenanthridines with H2O2as a sustainable oxidant
Duan, Chunying,Jin, Yunhe,Meng, Changgong,Wang, Lifang,Zhang, Qingqing,Zhang, Yongqiang
supporting information, p. 6926 - 6930 (2021/09/28)
The visible light-induced metal-free C(sp3)-H phenanthridinylation of simple alkanes with isonitrile is developed with H2O2as a terminal green oxidant. This reaction features good yields and selectivities, mild conditions, and a broad substrate scope with gaseous alkanes involved, allowing practical access to valuable alkyl-substituted phenanthridine derivatives.
Visible-Light-Mediated Direct Decarboxylative Acylation of Electron-Deficient Heteroarenes Using α-Ketoacids
Manna, Sabyasachi,Prabhu, Kandikere Ramaiah
, (2019/05/08)
Acylation of electron-deficient heteroaromatic compounds has been developed using visible light. α-Ketoacids have been used as an efficient source of acyl radicals under photoredox conditions. The in situ generated acyl radicals from α-ketoacids have been coupled to a wide variety of electron-deficient heteroaromatic compounds in a Minisci type reaction. This method would be attractive to access biologically attractive molecules.
Visible-Light-Initiated, Photocatalyst-Free Decarboxylative Coupling of Carboxylic Acids with N-Heterocycles
Zhang, Xiao-Yu,Weng, Wei-Zhi,Liang, Hao,Yang, Hua,Zhang, Bo
supporting information, p. 4686 - 4690 (2018/08/09)
A general and efficient protocol for direct C-H alkylation and acylation of N-heterocycles, using readily accessible carboxylic acids as radical precursors under visible-light irradiation without a photocatalyst and an additional acid additive, has been d
Photoredox-Catalyzed Decarboxylative C-H Acylation of Heteroarenes
Jia, Wei,Jian, Yong,Huang, Binbin,Yang, Chao,Xia, Wujiong
supporting information, p. 1881 - 1886 (2018/08/28)
A mild, environmentally friendly, and regioselective acylation of heterocycles with inexpensive carboxylic acids is reported via photoredox catalysis. The strategy is highlighted with good functional group tolerance and substrate scope which could rapidly
Synthesis of 6-aroyl phenanthridines by Fe-catalyzed oxidative radical cyclization of 2-isocyanobiphenyls with benzylic alcohols
Nie, Ziyi,Ding, Qiuping,Peng, Yiyuan
, p. 8350 - 8357 (2016/12/02)
A practical method for the synthesis of 6-aroyl phenanthridine derivatives by Fe-catalyzed oxidative radical cyclization of 2-isocyanobiphenyls with benzylic alcohols is described. In addition, this cyclization could be occurred by using toluene as aroyl source. The procedure tolerates various functional groups under simple conditions. A single-electron-transfer pathway is proposed according to mechanistic studies.
N-alkoxyheterocycles as irreversible photooxidants
Wosinska, Zofia M.,Stump, Faye L.,Ranjan, Rajeev,Lorance, Edward D.,Finley, Genita N.,Patel, Priya P.,Khawaja, Muzamil A.,Odom, Katie L.,Kramer, Wolfgang H.,Gould, Ian R.
, p. 313 - 328 (2014/04/03)
Irreversible photooxidation based on N-O bond fragmentation is demonstrated for N-methoxyheterocycles in both the singlet and triplet excited state manifolds. The energetic requirements for bond fragmentation are studied in detail. Bond fragmentation in t
Regiospecific Minisci acylation of phenanthridine via thermolysis or photolysis
Cheng, Pi,Qing, Zhixing,Liu, Sheng,Liu, Wei,Xie, Hongqi,Zeng, Jianguo
supporting information, p. 6647 - 6651 (2015/01/08)
In this study, a new type of Minisci reaction for regiospecific acylation of phenanthridine has been developed based on cross dehydrogenative coupling (CDC) strategy. Using substoichiometric amount of TBAB (tetrabutylammonium bromide, 30 mol %) and K2S2O8 as an oxidant, acyl radicals generate from aldehyde substrates under thermal conditions followed by a regiospecific intermolecular acylation with phenanthridine. Furthermore, a preliminary research has indicated that the acylation reaction can be carried out at room temperature when K2S2O8/TBAB is displaced by (NH4)2S2O8 and another 5 mol % of fac-Ir(ppy)3 is used as photocatalyst under irradiation of visible light. This intermolecular acylation reaction provides an easy access to 6-acylated phenanthridine derivatives.
